Compound G is a naturally occurring aromatic compound that is present in raspberries - CIE - A-Level Chemistry - Question 5 - 2012 - Paper 1
Question 5
Compound G is a naturally occurring aromatic compound that is present in raspberries.
(a) Identify the functional groups present in compound G.
(b) Complete the fo... show full transcript
Worked Solution & Example Answer:Compound G is a naturally occurring aromatic compound that is present in raspberries - CIE - A-Level Chemistry - Question 5 - 2012 - Paper 1
Step 1
Identify the functional groups present in compound G.
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Answer
The functional groups present in compound G are a hydroxyl group (-OH) and a carbonyl group (C=O). Additionally, the compound includes an aromatic ring, specifically a phenolic structure.
Step 2
Complete the following table with information about the reactions of the three stated reagents with compound G.
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reagent
observation
structure of organic product
type of reaction
sodium metal
effervescence/bubbles
redox
aqueous bromine
decolourises/white ppt.
electrophilic substitution
aqueous alkaline iodine
yellow ppt.
oxidation
Step 3
Draw the structures of the amine J and the intermediate K in the boxes above.
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Structure of Amine J
Amine J is a primary amine with a general formula of R-NH2.
Structure of Intermediate K
Intermediate K has a sulfonamide group attached to the aromatic ring.
Step 4
Suggest reagents and conditions for step 1.
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Step 1: The reagents used are sodium nitrite (NaNO2) with hydrochloric acid (HCl) or nitric acid (HNO2), carried out at temperatures below 10°C.
Step 5
Suggest reagents and conditions for step 2.
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Step 2: The reaction involves adding Intermediate K to a solution of compound G in aqueous NaOH.
Step 6
Suggest a reaction scheme by which compound G and propanoic acid could be converted into compound L.
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The reaction scheme can include the following steps:
Condensation of compound G with propanoic acid in the presence of a catalyst such as sulfuric acid (H2SO4).
